Hydrochloric Acid → alpha-[(1-Methylethylamino)methyl]-beta-Phenoxy-Benzeneethanol

HRID 1759533ノート

反応式

HRID 1759533 の反応式
B.O1CCCC1.[OH:7][CH:8]([CH:15]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=O.Cl.O>[Na+].[Cl-].O1CCCC1>[CH3:14][CH:12]([NH:11][CH2:9][CH:8]([OH:7])[CH:15]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH3:13]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962Water2 回HCID 2723981Borane;tetrahydrofuranHCID 13041337alpha-Hydroxy-beta-Phenoxy-N-(1-Methylethyl)Benzenepropanamide

生成物 1

HCID 13041349alpha-[(1-Methylethylamino)methyl]-beta-Phenoxy-Benzeneethanol

試薬・触媒・溶媒 2

HCID 5234Sodium Chloride溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Borane-tetrahydrofuran complex (1 M solution in tetrahydrofuran, 20 ml.) was transferred by a syringe to a 100 ml. three-neck flask equipped with a reflux condenser, a nitrogen gas inlet and a rubber septum. The reaction flask was then chilled in a mixture of ice and table salt. α-Hydroxy-β-phenoxy-N-(1-methylethyl)benzenepropanamide (1.9 g.) suspended in tetrahydrofuran (25 ml.) was added slowly keeping the temperature at ca. 0°. The solution thus obtained was brought to reflux and maintained there for 2.5 hours. The reaction mixture was cooled to room temperature, dilute hydrochloric acid (6 N HCl 3 ml.) and water (5 ml.) was added carefully, and the mixture was heated under reflux for 20 minutes. It was then evaporated on a rotary evaporator under reduced pressure to give a solid residue. The residue was treated with water. The water insoluble material was separated by collecting on a filter and washed with water. The filtrate and washings were combined and made alkaline by addition of 50% aqueous sodium hydroxide solution, then extracted with chloroform 3 times. The combined extract was dried over magnesium sulfate, and evaporated under reduced pressure to give an oil which solidified on standing. The crude product was recrystallized from ether and petroleum ether, giving 1.0 g. of product, m.p. 95°-96°.

後処理

  1. customthree-neck flask equipped with a reflux condenser, a nitrogen gas inlet
  2. additionwas added slowly
  3. customat ca. 0°
  4. customThe solution thus obtained
  5. temperatureto reflux
  6. temperaturemaintained there for 2.5 hours
  7. temperaturethe mixture was heated
  8. temperatureunder reflux for 20 minutes
  9. customIt was then evaporated on a rotary evaporator under reduced pressure
  10. customto give a solid residue
  11. customThe water insoluble material was separated
  12. customby collecting on
  13. filtrationa filter
  14. washwashed with water
  15. additionby addition of 50% aqueous sodium hydroxide solution
  16. extractionextracted with chloroform 3 times
  17. extractionThe combined extract
  18. dry with materialwas dried over magnesium sulfate
  19. customevaporated under reduced pressure
  20. customto give an oil which
  21. customThe crude product was recrystallized from ether and petroleum ether
  22. customgiving 1.0 g

出典と根拠

ORDレコード
ord-35b3964f361a4510961e8a19eef4b0c6
出典データセット
uspto-grants-1982_07
特許番号
US04341718

反応ノート

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